The Other, Other Playboy.

When is a chukka more than just a chukka? When it’s a Playboy. No, not that Playboy, I’m talking about the chunky-soled ankle boots that became legendary thanks to that other playboy, Steve McQueen. During his sixties heyday, McQueen was inescapable both on-screen and off, and when he was snapped lounging by the California coast, or jetting around town with whatever starlet he was seeing that week, he was oft wearing a hefty pair of chocolate suede chukkas with a big ol’ crepe sole.

Like a desert boot on a jacked up sole, Playboys were forever tied to McQueen’s style, but they never quite caught on here in America. Recently though, as the refined yet casual look of English footwear has caught on here in post-aughts America, Playboys have been steadily growing in popularity.

While Northampton shoemakers like Sanders have produced Playboys for decades, it was Mark McNairy who really made the boots accessible stateside by offering them as part of his New Amsterdam line. This once elusive boot is now just a few clicks away and if you’re wondering just how versatile such a thick-soled shoe can be, well I’ll let these photos of the King of Cool handle that one. â€”JG

Comments on “The Other, Other Playboy.”

Take a ride up to Harlem. A lot of old-school players wear these when it’s time to let the gators rest.

Matthew Pikeon November 21, 2013@ 6:05 PM:

I’ve seen a few over here, I must say they look comfier than actual desert boots.

Coryon November 22, 2013@ 2:52 PM:

I’m a big fan of Clarks desert boots. I was wearing a pair recently while shopping at a local mall. An older gentleman, probably in his 60s, came up to me and asked, “Where did you get those? I haven’t seen those kinds of shoes in years! I used to love those.”
There just happen to be a Clarks store at this mall, so I pointed him in that direction and watched as he walked in. We both were smiling ear to ear. I hope he came away with a new pair of boots and a head full of nostalgic memories.

RichardMon November 22, 2013@ 10:52 PM:

I agree with Jules. During the 60’s to early 70’s, Playboy’s were the standard hang-out shoe for brothers all over the city. They were worn with mohair/silk pants and colorful alpaca sweaters or your Lee jeans. White wool (not cotton) crew socks was a must when you wore them with your jeans. They came in at least have dozen colors in High (chukka) and Low (oxford).

Tim Walkeron November 27, 2013@ 1:30 PM:

The Sanders crepe soled shoes are incredibly comfortable and beautifully lined. Fantastic value for money for a Northamptonshire made shoe also.